Cinnamamids



i atented Dec. 13, 1938 PATENT OFFiCE CINNAMAMIDS William A. Lott, East Orange, N. J., assignor to E. R. Squibb & Sons, New York, N. Y., a corporation of New York No Drawing. Original application September 12, 1933, Serial N0.

689,158, now Patent No.

2,103,265. Divided and this application May 8, 1937, Serial No. 141,568

4 Claims.

/alkyl H5 o H: c c ONHalkylene-N alkyl alkyl and the salts thereof. These compounds, which are characterized by valuable local-anesthetic properties, may be prepared by causing the appropriate cinnamyl chloride to react with the appropriate diamine.

Examples 1. N a ethyl cinnamyl N diethyl ethylene diamine hydrochloride. A solution of 11.5 g. of methyl cinnamyl chloride in 25 cc. of benzene is gradually added to a solution of 6.9 g. of unsymmetrical diethyl ethylene diamine in 50 cc. of dry benzene, and the reaction mixture is cooled to room temperature; and the copious yellow precipitate is washed several times with dry benzene and once with dry acetone. There remains the compound sought, in the form of snow-white crystals having a melting point of 162.5-163.5 C. and dissolving readily in water.

2. N-a-methyl-cinnamyl N-diethyl ethylene diamine hydrochloride. 8.0 g. of u-methyl cinnamyl chloride dissolved in 30 cc. of absolute ether is refluxed for three hours with a solution of 3.9 g. of diethyl ethylene diamine in 30 cc. of

anhydrous ether; the crystalline product, which is the desired compound, is separated by filtration, and after recrystallization from acetone is in the form of white crystals melting at 111-112.5 C.

3. N-a-amyl-cinnamyl N-diethyl ethylene diamine hydrochloride. A solution of 5 g. of u-amyl cinnamyl chloride in 15 cc. anhydrous ether is added to a. solution of 1.8 g. of unsymmetrical diethyl ethylene diamine in 15 cc. anhydrous ether, and the mixture is refluxed for about an hour; on cooling, the compound sought separates as white crystals, which, after being washed several times with anhydrous ether, melt at 84-95 C.

It is to be understood that the foregoing examples are merely illustrative and by no means limitative of the invention, which may be variously otherwise embodied-as with respect to particular compositions and processesWithi-n the scope of the appended claims.

I claim:

1. Compounds of the group consisting of alkyl C 6115 O H: C O ONEalkylene-N z ilkyl and the inorganic salts thereof.

2. Na-ethyl-cinnamyl' N '-diethyl ethylene diamine hydrochloride.

3. N-a-methyl-cinnamyl N-diethyl ethylene diamine hydrochloride.

4. N-a-amyl-cinnamyl N-diethyl ethylene diamine hydrochloride.

alkyl WILLIAM A. LOTT. 

